WO2007137021A2 - Catalyseurs comprenant une combinaison de métaux oxydés et procédé de clivage d'hydropéroxydes de phénylalkyle faisant intervenir lesdits catalyseurs - Google Patents

Catalyseurs comprenant une combinaison de métaux oxydés et procédé de clivage d'hydropéroxydes de phénylalkyle faisant intervenir lesdits catalyseurs Download PDF

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Publication number
WO2007137021A2
WO2007137021A2 PCT/US2007/068860 US2007068860W WO2007137021A2 WO 2007137021 A2 WO2007137021 A2 WO 2007137021A2 US 2007068860 W US2007068860 W US 2007068860W WO 2007137021 A2 WO2007137021 A2 WO 2007137021A2
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WO
WIPO (PCT)
Prior art keywords
cleavage
metal
catalyst
phenylalkyl
feed
Prior art date
Application number
PCT/US2007/068860
Other languages
English (en)
Other versions
WO2007137021A3 (fr
Inventor
Narayana Mysore
John Charles Saukaitis
John Anthony Smegal
Original Assignee
Shell Oil Company
Shell Internationale Research Maatshappij B.V.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Oil Company, Shell Internationale Research Maatshappij B.V. filed Critical Shell Oil Company
Priority to US12/300,840 priority Critical patent/US8026398B2/en
Publication of WO2007137021A2 publication Critical patent/WO2007137021A2/fr
Publication of WO2007137021A3 publication Critical patent/WO2007137021A3/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • B01J37/0207—Pretreatment of the support
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/002—Mixed oxides other than spinels, e.g. perovskite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/14—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of germanium, tin or lead
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/18—Arsenic, antimony or bismuth
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/24—Chromium, molybdenum or tungsten
    • B01J23/30—Tungsten
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/24—Chromium, molybdenum or tungsten
    • B01J23/31—Chromium, molybdenum or tungsten combined with bismuth
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/85—Chromium, molybdenum or tungsten
    • B01J23/888—Tungsten
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • B01J37/0205—Impregnation in several steps
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Definitions

  • Hydroxybenzenes have a wide variety of industrial uses. A number of processes are currently available for the production of hydroxybenzenes. One such process is known as a "cumene process.”
  • Dropwise addition of cumene hydroperoxide into a relatively large volume of diluent may produce a number of advantages.
  • the drops of cumene hydroperoxide are expected rapidly to convert to phenol and acetone after addition to the large volume of diluent, and the accumulation of less desirable byproducts (cumyl phenol, dimers of AMS) should be minimized or avoided.
  • the present application provides a catalyst comprising a combination of oxidized metals.
  • the present application also provides a catalyst comprising oxidized forms of a combination of metals selected from the group consisting of: tungsten and tin; tungsten and iron; tungsten and cerium; tungsten and bismuth; tungsten and zinc; zirconium and tin; and, antimony and tin.
  • the present application provides a process for cleaving phenylalkyl hydroperoxides using catalyst comprising a combination of oxidized metals.
  • the present application also provides a process for cleaving phenylalkyl hydroperoxides comprising: feeding a phenylalkyl hydroperoxide feed and a ketone feed to a reactor in a continuous process to produce a cleavage reaction mixture, the reactor containing catalyst comprising a combination of oxidized metals; and, subjecting the cleavage reaction mixture to cleavage conditions in the presence of the catalyst, the cleavage conditions being effective to cleave phenylalkyl hydroperoxide and to produce a cleavage product comprising one or more hydroxybenzenes and one or more ketones.
  • Figure 1 is a schematic diagram of an adaptation of the reactor system used in Example 18.
  • FIG. 2 is a schematic diagram of another reactor system suitable for practicing the method described herein.
  • the present application provides catalysts comprising a combination of oxidized metals.
  • the catalysts are useful to cleave phenylalkyl hydroperoxides, even at relatively high concentrations. Cleavage of phenylalkyl hydroperoxides using catalysts comprising a combination of metals produces a number of advantages when compared to the use of dilute sulfuric acid to cleave the phenylalkyl hydroperoxides.
  • Advantages include, but are not necessarily limited to: minimizing handling of hazardous liquid acids; eliminating a neutralization step; reducing the water content of the neutralized reaction solution; reducing the energy cost of boiling additional water; removing corrosive salts from the reaction mixture; increasing the yield of desired products; minimizing impurities; reducing equipment costs required to run the process; reducing operating costs; and, minimizing unwanted hydroxyketones and ketone condensation products.
  • Phenylalkyl hydroperoxides which may be cleaved using the catalysts have the following general structure:
  • R and R 1 independently are selected from the group consisting of hydrogen and alkylene groups having 1 or more carbon atoms, preferably 5 carbon atoms or less, wherein R and R 1 optionally may be linked together to form a ring structure; and R 2 and R 3 independently are selected from the group consisting of hydrogen, hydroxyl groups, and alkyl groups having from about 1 to 4 carbon atoms. In one embodiment, R 2 and R 3 are selected from the group consisting of hydrogen and 100 methyl groups.
  • R 2 and R 3 groups having 2 carbon atoms or more could attain various levels of oxidation.
  • R 2 and R 3 groups having 2 carbon atoms or more could oxidize to the corresponding hydroperoxides and be cleaved to hydroxybenzene and the corresponding ketones.
  • R 4 and R are alkyl groups having 1 or more carbon atoms, preferably having 6 130 carbon atoms or less.
  • R 4 and R 5 also may be joined to form a ring.
  • R 4 and R are joined to form cyclohexanone.
  • Hydroxybenzenes in the cleavage product generally have the following structure:
  • Phenylalkenes which may be byproducts in the cleavage product have the following general structure: 140
  • Phenylalkyl ketones present as byproduct in the cleavage product generally have the following structure:
  • R 13 , R 14 , R 15 , and R 16 are the same or different, and are selected from the group consisting of alkyl groups having 1 carbon atom or more, preferably having 5 carbon atoms or less, depending upon the phenylalkyl hydroperoxides, wherein a combination selected from the group consisting of (a) R 13 and R 14 and (b) R 15 and
  • R 21 and R 22 also are hydrogen
  • the phenylalkyl alcohol is ethylmethyl benzyl alcohol (EMBA), which has the
  • the first metal is selected from the group consisting of tin, zinc, cerium, and combinations thereof
  • the second metal is selected from the group consisting of tungsten, zirconium, and combinations thereof.
  • the catalysts comprise oxidized forms of a combination of metals selected from the group
  • oxidized metals have less of a tendency to dissolve in the cleavage reaction mixture.
  • Catalyst comprising oxidized tin and oxidized zirconium has the advantage that it has less of a tendency to dissolve in the cleavage reaction mixture.
  • the catalyst may be made according to the methods described in U.S. Patent No. 6,169,215, incorporated herein by reference. Generally, the method involves calcining a source of the first metal with a source of a second metal at a temperature of 400 0 C or more.
  • suitable supports include but are not necessary limited to silica, alumina, silica-alumina, titania, zirconia, zeolites, and acidic clays.
  • suitable zeolites include, but are not necessarily limited to zeolite beta and zeolites having a Constraint Index of from 1 to 12.
  • suitable acidic clays include, but are not
  • 235 necessarily limited to kaolinite, attapulgite, montmorillonite, and cloisite clays.
  • Supported oxidized metals may be made using a variety of methods and may comprise a variety of structures. Suitable methods of preparation include, but are not necessarily limited to impregnation, coimpregnation, including single or multiple impregnations, coprecipitation, physical admixture or any other suitable method.
  • supported catalysts comprising a combination of oxidized metals are prepared by precipiting sources of a combination of metals onto the support, separately or in the same procedure.
  • Suitable sources of metals for precipitation include, but are not necessarily limited to metal nitrates,
  • the catalyst After calcination, the catalyst comprises a combination of a first amount of a first
  • the combination has sufficient acidity to cleave the phenylalkyl hydroperoxide.
  • the acidity of the combination is greater than that of a mixture formed by separately oxidizing the first metal and the second metal and subsequently mixing the first amount of the oxidized first metal with the second amount of the oxidized second metal.
  • the phenylalkyl hydroperoxide feed comprises from about 70 wt.% to about 90 wt.% phenylalkyl hydroperoxides. In yet another embodiment, the phenylalkyl hydroperoxide feed comprises 80 wt.% or more phenylalkyl hydroperoxide. In one embodiment, the phenylalkyl hydroperoxide feed comprises from about 80 wt.% to about 88 wt.% phenylalkyl hydroperoxide, based on the total weight of the cleavage feed.
  • the ketone feed rate is from about 0.1 wt.% to about 10 wt.% based on the phenylalkyl hydroperoxide feed rate. In one embodiment, the ketone feed rate is about 10 wt.% based on the phenylalkyl hydroperoxide feed rate. In other words, where the phenylalkyl hydroperoxide feed rate is 1 gram or less of phenylalkyl hydroperoxide feed per gram of catalyst per hour, the ketone feed rate is from
  • the ketone feed rate is about 0.1 gram of ketone feed per gram of catalyst per hour.
  • the relatively mild cleavage conditions increase the concentration of di(phenylalkyl)peroxide in the cleavage product relative to the amount of di(phenylalkyl)peroxide in the cleavage feed.
  • the cleavage product comprises from about 1 wt.% to
  • EXAMPLE 3 146.05 grams of Zn( ⁇ 2 CCH 3 ) 2 '2H 2 O were dissolved with stirring in 28 grams of deionized water. 30 grams of silica extrudate obtained from CRI was impregnated with the solution and allowed to age for 1 hour. The Zn-impregnated silica was dried and the solvent evaporated in an oven at 150° C for 3 hours. The dried Zn- impregnated silica was impregnated with a solution containing 5.06 grams of ammonium metatungstate in 30
  • the product contained the following wt.% of the following components, based on the total weight of the cleavage product: 0.16 wt.% acetophenone; less than 0.4 wt.% ⁇ -methylstyrene; less than 0.5 wt.% DMBA; 0.02 wt.% or less cumyl phenol; and 1.0 wt.% or less dicumylperoxide.
  • the following Table shows the composition (wt. %) of the cleavage solution at 0 minutes, 60 minutes, and 120 minutes after completion of addition. The results show 100% conversion of cumene hydroperoxide.
  • the product contained the following components in wt.%, based on the total weight of the cleavage product: less than 0.5 wt.% 645 ⁇ -methylstyrene (and dimers); only 0.13 wt.% acetophenone; and, less than 0.5 wt.% DMBA.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un catalyseur qui comprend une combinaison de métaux oxydés et des procédés de clivage d'hydropéroxydes de phénylalkyle en présence dudit catalyseur.
PCT/US2007/068860 2006-05-16 2007-05-14 Catalyseurs comprenant une combinaison de métaux oxydés et procédé de clivage d'hydropéroxydes de phénylalkyle faisant intervenir lesdits catalyseurs WO2007137021A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/300,840 US8026398B2 (en) 2006-05-16 2007-05-14 Catalysts comprising a combination of oxidized metals and a method for cleaving phenylalkyl hydroperoxides using the catalysts

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US74736106P 2006-05-16 2006-05-16
US60/747,361 2006-05-16

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WO2007137021A2 true WO2007137021A2 (fr) 2007-11-29
WO2007137021A3 WO2007137021A3 (fr) 2008-04-10

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
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US8026398B2 (en) 2011-09-27
US20100063326A1 (en) 2010-03-11
WO2007137021A3 (fr) 2008-04-10

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